[3-(diphenylphosphanyl)propyl]diphenylphosphane

• ChemBase ID: 70560
• Molecular Formular: C27H26P2
• Molecular Mass: 412.442862
• Monoisotopic Mass: 412.15097409
• SMILES: C(CCP(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: C(CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2
• InChIKey: LVEYOSJUKRVCCF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(diphenylphosphanyl)propyl]diphenylphosphane
• IUPAC Traditional name: [3-(diphenylphosphanyl)propyl]diphenylphosphane
• Synonyms: dppp; 1,3-Bis(diphenylphosphino)propane; 1,3-Bis(diphenylphosphino)propane; [3-(diphenylphosphanyl)propyl]diphenylphosphane; 1,3-双(二苯基膦)丙烷; 1,3-双(二苯基磷烷基)丙烷

Database IDs

• CAS Number: 6737-42-4
• EC Number: 229-791-2
• MDL Number: MFCD00003050
• Beilstein Number: 2821785
• PubChem SID: 24855854; 162036275
• PubChem CID: 81219
• CHEMBL: 73394
• Chemspider ID: 73276
• Wikipedia Title: 1,3-Bis(diphenylphosphino)propane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.1541
• LogD (pH = 7.4): 7.1541
• Log P: 7.1541
• Molar Refractivity: 126.3902 cm^3
• Polarizability: 50.2117 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chlorocarbons in water
• Apperance: white solid
• Melting Point: 58-63°C; 63 - 65°C; 63-65 °C(lit.)
• Hydrophobicity(logP): 7.387
• Ligand For: Carbonylations; C-C Bond Formation; Negishi Coupling; Sonogashira Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Air Sensitive; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39; 26-37-60
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (C6H5)2PCH2CH2CH2P(C6H5)2

DETAILS

Sigma Aldrich - 262048

Packaging
1, 5, 25 g in glass bottle

REFERENCES

• Chelating phosphorus ligand which forms a 1:1 complex with NiCl₂, which is an efficient catalyst for the coupling of Grignard reagents with aryl, vinylic or heterocyclic halides: Bull. Chem. Soc. Jpn.,49, 1958 (1976); Tetrahedron, 38, 3347 (1982); Synthesis, 386 (1988).
• Successful Suzuki coupling of arylboronic acids with aryl chlorides bearing electron-withdrawing groups was achieved in the presence of Palladium(II) acetate, 10516, and dppp: Tetrahedron Lett., 38, 5575 (1997).